An ursolic acid is a pentacyclic triterpene acid compound which is possible to be extracted from natural products such as rosemary leaves, and the like. The ursolic acid is regarded as a natural product-derived compound contained in various plants such as apples, particularly, bark, lavender, basil, rosemary, olegano, thyme, and the like.
The ursolic acid may be represented by Chemical Formula 1 below, and may be referred to as a chemical name: 3β-hydroxy-urs-12-en-28-oic acid. The ursolic acid has a molecular weight of about 456.68 and has a general formula of C30H48O3.

As shown in Chemical Formula 1 above, the ursolic acid has a basic structure of pentacyclic triterpene, and has a hydroxyl group at C-3 position, a double bond at C-12 position, and a carboxylic acid at C-28 position. It is known that the ursolic acid having the above-described structure is very poorly water-soluble, and is an optically active material having a significantly complicated structure including 10 chiral carbons.
Due to these characteristics, the ursolic acid is not possible to be chemically synthesized, and it is known that these materials are obtainable only by extraction and purification from the natural products such as plants, and the like, containing the ursolic acid in a large amount. However, since a content of the ursolic acid contained in the natural products such as plants, and the like, is not large, a significantly high cost is required to obtain the ursolic acid having high purity and high concentration by the extraction and the purification.
Meanwhile, the above-described ursolic acid is known as a functional cosmetic material. In particular, it has been reported that the ursolic acid is usable for skin improvement regarding photoaging and inflammation treatment. Meanwhile, the ursolic acid used as the functional cosmetic material generally has low purity and contains an oleanolic acid which is a structural isomer having hydrogen at C-29 position and dimethyl at C-30 position, and the like. Therefore, it is difficult to apply the low purity ursolic acid used as the cosmetic material as it is, for pharmaceutical usage.
Nevertheless, there are a number of reports that the ursolic acid is capable of being applied to various pharmaceutical products. For example, it has been reported that the ursolic acid inhibits NF-KB activation in living cells to enhance an efficacy of anti-cancer treatment-chemotherapy (see Int. J. Cancer (2010), 127, 462˜473).
In addition, it has been reported that the ursolic acid exhibits excellent efficacy for treating and preventing muscle atrophy (see Cell Metabolism (2011) 13, 627˜638). Besides, it has been reported that the ursolic acid is used in treatment of hepato fibrosis (see J of Hepatology (2011) 55, 379˜387), and it has been known that the ursolic acid has a possibility of being used in treatment of hyperlipidemia by activating PPAR-α (see Bioorg Med Chem Lett (2011) 21, 5876˜5880).
In addition, some research into an ursolic acid derivative capable of more enhancing efficacy of the ursolic acid or having new efficacy has been made.
For example, an ursolic acid derivative having phosphate at C-3 position is disclosed in EP1889850A1, and a derivative in an amine salt form obtained by combining a carboxylic acid at C-28 position of the ursolic acid with piperazine, and the like, is disclosed in U.S. Pat. No. 3,909,089. In addition, a derivative having a carboxy propionyloxy group at C-3 position of the ursolic acid and exhibiting activity as an anti-ulcer agent is disclosed in U.S. Pat. No. 4,530,934. Further, an ursolic acid derivative having an acyloxy group at C-3 position and a C5 to C8 alkyl group substituted for the carboxyl group at C-28 position is disclosed in US2011/0190388A1, wherein the ursolic acid derivative is usable as an anti-inflammatory agent and anti-cancer agent.
Even through the ursolic acid or derivatives thereof have various pharmacokinetic availabilities and efficacies as described above, research into formulation containing the ursolic acid has a limitation since the ursolic acid has poor water-solubility and extremely low oral absorptivity, for example, less than 1% and it is difficult to prepare a high purity ursolic acid.